Spirobenzofuran
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| Category | Antibiotics |
| Catalog number | BBF-02929 |
| CAS | |
| Molecular Weight | 262.30 |
| Molecular Formula | C15H18O4 |
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Description
It is produced by the strain of Acremonium sp. HKI 0230. It has moderate activity against gram-positive bacteria such as Bacillus subtilis with MIC of 25 μg/mL. It has no effect against gram-negative bacteria and fungi.
Specification
| Synonyms | 2,5-dihydroxy-2',2',6-trimethyl-2H-spiro[benzofuran-3,1'-cyclopentan]-4'-one |
| IUPAC Name | 2,5-dihydroxy-4',4',6-trimethylspiro[2H-1-benzofuran-3,3'-cyclopentane]-1'-one |
| Canonical SMILES | CC1=CC2=C(C=C1O)C3(CC(=O)CC3(C)C)C(O2)O |
| InChI | InChI=1S/C15H18O4/c1-8-4-12-10(5-11(8)17)15(13(18)19-12)7-9(16)6-14(15,2)3/h4-5,13,17-18H,6-7H2,1-3H3 |
| InChI Key | GASOCDUVJSYZGK-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in Methanol |
Reference Reading
1. Total syntheses of (+)-adunctins C and D: assignment of their absolute configurations
Jian Xiao, Jun Zhao, Ya-Wen Wang, Gan Luo, Yu Peng Org Biomol Chem. 2021 Nov 25;19(45):9840-9843. doi: 10.1039/d1ob02055b.
The first total synthesis of (+)-adunctin C (ent-1) and (+)-adunctin D (2), two monoterpene-substitued dihydrochalcones isolated from Piper aduncum (Piperaceae), was achieved. A regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (-)-β-phellandrene was developed to construct their unique spirobenzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors.
2. Diastereoselective synthesis of chroman bearing spirobenzofuranone scaffolds via oxa-Michael/1,6-conjugated addition of para-quinone methides with benzofuranone-type olefins
Hongmei Qin, Qimei Xie, Long He RSC Adv. 2022 Jun 6;12(26):16684-16687. doi: 10.1039/d2ra03031d. eCollection 2022 Jun 1.
A simple and convenient cyclization of ortho-hydroxyphenyl-substituted para-quinone methides with benzofuran-2-one type active olefins via oxa-Michael/1,6-conjugated addition has been developed, which afforded an easy access to enriched functionalized chroman-spirobenzofuran-2-one scaffolds with good to excellent yields (up to 90%) and diastereoselectivities (up to >19 : 1 dr). This reaction provided an efficient method for constructing desired spirocyclic compounds combining both well-known heterocyclic pharmacophores chroman and benzofuran-2-one.
3. Catalyst-Controlled Selectivity Switch in Three-Component Reaction: An NHC-Catalyzed Strategy for the Synthesis of δ-Lactone-Fused Spirobenzofuran-3-ones
Zhanyong Wang, Ting Yang, Dongfang Liu, Rongxiang Chen, Nan Wang, Hong Liu, Jiarong Li, Kaikai Wang, Hongxin Liu Molecules. 2022 Sep 13;27(18):5952. doi: 10.3390/molecules27185952.
An efficient, three-component reaction of aldehydes and benzofuran-3-ones was developed. This process provides a new approach for the preparation of synthetically and biologically important spirobenzofuran-3-one derivatives with moderate-to-good yields under mild conditions. A switch of intramolecular to intermolecular domino Michael-aldol-lactonization leading to differential product formation was achieved by different NHCs catalysis.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
